I very much agree Night, I think what your describing is EXACTLY the point I'm at in life right now; Im trying to figure out how I can live a grown up life, paying my bills and having my own place to stay, but doing it with an income from my creative work.
An important aspect of it is that being an indie creative is a calling, there is no easy rout. I tried the traditional 9-5 office job and renting a trendy apartment in the past and I learned I could not life that way, I had to make my own things.
Ice, I totally agree with you too, and Id love to say who cares about money, but I also enjoy foood!

One big challenge is that no creative person should be forced to engage with a community to support their work, being a people person and being creative are things that don't really mix so well (just think how many great artists were very hard to get along with); with that in mind promoting your work on social media is very wrong for many people. I find I'm able to switch my brain between community mode and creating mode, but not everyone can do that.
I suppose the question really boils down to how do you convert your work into cash?
This internet is great for mass popularity support and niche interests support, but both of those are community centric. They depend on you being able to reach out to a group of people and engage them enough to support your work, essentially its like being an entertainer as much as a creative.
That forces creatives to monetize everything, sell perks and packs and upgrades and that kinda stuff. 99.99% of people wont support something (ether financially or with likes/follows) unless they think they will get something in return. What people don't really think of is that they were already getting something when it was free.
If I started to paywall gifypet I think Id become the most unpopular person on neocities overnight

Its been praised and quoted and linked so often though it makes me feel good and that's a kind of payment. MoMG on the other hand gets very little attention, I think if that was my only web project I would feel very depressed about it; so there is a hard value to visible engagement even if its not money.
Being an indie creative can be lonely too, sometimes I'll work away on something for a week and the only praise I get is the one or two likes I get on the neocities update feed. Perhaps the issue is that the internet is a wonderful publishing tool, but it makes it too easy for you to hyper focus on your tiny area of life; when in reality what you really need is to build a broader real life community. I found I had that community in college, but outside colleges and jobs, that structure is hard to find.
Getting more practical on indie projects though; I think its very much about not putting all your eggs in one basket. Don't just make one thing and expect it to support you. Make a free thing, and a paid thing and a web thing and a physical thing. Show it on your site and on the web, but also talk to real people about it even if that audience seems a lot smaller its a different kind of audience. Iv been focusing a lot on local arts applications to help fund my next 3d worlds projects, Iv no idea if that will work out, but it might!
You seem to bounce around the idea of projects and indie life Night? Are you working full time at a job now and considering going indie? Or have you tried in the past? Have I asked you this before and forgotten?

Holy nelly iv been writing this for ages, I had other posts I wanted to write before bed!!!